11 Best Hotels in Chianti Tuscany

Nestled between Siena and Florence, Chianti is the epitome of the charm and beauty of Tuscany. Stretching more than 100 mi (161 km), the region is famed for historic estates, scenic vineyards, and rolling, undulating hills. So, it’s not surprising that it has as many as 8 wine subregions with hundreds of winegrowers producing some of the finest wines in the world. The best hotels in Chianti, Tuscany, are an extension of its winemaking soul, but with a stunning blend of rich heritage and modern creature comforts. What’s more, they range from classic, luxurious winery hotels to smaller, family-run boutique stays and vineyard villages, where everyone has been making wine for centuries.

Not only do they have guided tours and tasting sessions, but they also boast all contemporary luxuries that we expect from hotels; think infinity swimming pools, spas, and the like. So what are you waiting for? Here’s a well-rounded guide to the best stays in Chianti, Tuscany.

Borgo Scopeto Relais

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We begin with the stylishly converted historic hamlet of Borgo Scopeto Relais, which sits deep in the heart of southern Chianti. This 1200-acre estate has a remote, bucolic setting, and yet Siena is just half an hour away. So, the fact that the local hills were strewn with fairytale castles and noble wineries – Volpaia, Vertine, Meleto, and Brolio – was just perfect for us.

For a rural retreat, the amenities here were decidedly modern and luxurious: there was not only a fitness center but even a fantastic spa that also offered vino-therapy. After the spa, our favorite places to hang out were the two tranquil swimming pools, complete with daybeds and poolside services. For those who like a little bit of action, there are billiards tables, tennis courts, hiking tours, go-karting, Nordic walking, and tours. Of course, wine tasting in the cellars and dining and wining at the elegant restaurant and bar was something we all did. We could even hire vintage cars, Vespas, and mountain bikes. Please note that the relais is seasonal, and is shut from the end of November to early March.

We had the choice of 58 spacious and chic rooms and suites, each of which is individually styled with Chianti color palettes and contemporary furnishings. While some had direct garden access, many, including ours, had serene views of the Montagnola and Chianti hills. Minibars, flat-screen TVs, and luxuriously finished travertine and marble bathrooms with the relais’ own cosmetic range of bath products wrap up the features.

Villa Dievole Wine Resort

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Villa Dievole Wine Resort is probably one of the oldest wineries on this list — it’s been making wine, on and off, since 1090! Today, it’s not just a resort, but it’s also home to nearly 80 hectares of vineyards with a whopping 16 working vineyards! We were thrilled to be staying at this 18th-century Hamlet-turned-luxe wine estate, whose classic guided tours were one of the best in the region that we’d seen. They not only offered wine tastings but also olive oil tastings that they grew right on the property. Additionally, we loved indulging in cooking classes, swimming in, and lounging by one of the two lovely swimming pools. Dining at the signature, award-winning restaurant, Novecento, was a pleasure. Did you know that they even had bikes which we could simply borrow and explore the Tuscan countryside? Yes!

We loved the creamy dreamscape vibe of the rooms and suites at Dievole: think whitewashed ceilings, stone floors, marble bathrooms, and furnishings and linens in pale hues. Moreover, there were lovely pops of color in the form of the wall-mounted Medici-style still-lifes.

Borgo San Felice Resort Relais & Châteaux

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Most luxurious. We can’t have a list of the best stays somewhere and not mention a Relais & Chateaux property, can we? Welcome to Borgo San Felice Resort Relais & Châteaux, which sits on a hill in Chianti, Siena, and is surrounded by its own vineyards, parklands, and olive groves. We loved the poetic getaway vibe of this stunning country house hotel, which sat in the sun-kissed Piazza San Felice in a lovingly preserved and authentic Italian village. Choose from 33 sumptuously decorated and gorgeous rooms and suites, all of which had playful yet muted hues, draped linens, soft furnishings, huge windows with amazing views, and massive bathtubs in exquisite bathrooms.

What we loved was that we were surrounded by rows of immaculately tended vineyards, which produce some of the region’s most celebrated wines. In fact, wine is at the very core of this former working village-turned-resort, including the serene spa and two exceptional Mediterranean restaurants. Since it’s a wine estate, the hotel is home to a native species, Vigorello, which ended up producing the first-ever Super Tuscan wine from the estate. Additionally, there’s also the prized Sangiovese and Pugnitello grape varieties. Wine tastings aside, the hotel also had billiards and tennis courts, a lovely swimming pool, and wonderful views for miles — it’s heavenly.

Castello di Bibbione

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Best value for money. Step back in time at Castello di Bibbione, which is nestled in the Chianti countryside right outside the city of Florence. Originally built by the Cadolingi of Montecascioli, this stunning 10th-century estate and former fortress still dominates the hilltop and has a powerful vibe even today.

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Today, the place is more than just a castle in a tiny medieval village; it’s surrounded by olive groves, endless vineyards, and ancient homes. We had the choice of multiple apartments, and we stayed in one in the main farmhouse. However, they all boasted incredible views, including the stunning Villa Il Poggio, which has its own pool and private gardens. Nevertheless, they all boasted remnants of the original fortress as well as modern creature comforts.

One of the best bits of our stay here was getting to experience the property’s own olive oil and wine production. We spent a wonderful afternoon tasting wine and learning about the local vintages, even as we picked up some samples from the shop on the property. During sun-kissed days, we’d enjoy complimentary biking excursions followed by a swim in the swimming pool and lounge by it too. The gardens were also fabulous places to unwind and relax, especially since they also had alfresco seating and BBQ facilities. Did we mention that it was possible to book in-room massage treatments as well? Yep.

Castello di Meleto

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The magnificent Castello di Meleto is tucked away in the Chianti countryside. Its location is a beautiful and easy drive from Siena, Florence, and Arezzo, making it the perfect base for our Tuscan adventure and allowing us to explore it easily. The structure, which is perched high up on a hill, was first built in 1256 by Benedictine monks. So, it had centuries of history, but with a modern twist just for us.

We couldn’t help but feel the weight of the rich history here, especially since this fortress of a structure has survived 15th-century conflicts with almost no damage. However, it transformed into a peaceful villa in the 1700s, shedding its old defenses. We loved how balanced the restoration must have been, as the current vibe beautifully balances the old and the new. So, we found everything from exposed brick, original wooden beams, and towering walls to modern amenities. We’d spend hours relaxing by the incredible infinity pool with breathtaking valley views, digging into Tuscan delights at the Osteria di Meleto, and savoring local wines right on the property.

With just 11 bright and cozy rooms and suites to choose from, staying here felt intimate and exclusive. While the seven characterful ones lie in the castle, the four in the Canonica nearby were stylishly modern. So, the castle ones had vintage rugs, romantic four-posters, antiques, and updated bathrooms, while the Canonica and the farmhouse apartments were comfortable, with the latter even having its own pool.

Castello di Tornano Wine Relais

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Wining and dining doesn’t get any better than at Castello di Tornano Wine Relais, which is perched on a Tuscan hillside. So, we had stunning views of the Chianti Classico region from almost everywhere in the hotel, whether it was the restaurant, the rooms, or the common areas, like the pool.

Our stay here was all about exploring. Firstly, we loved trying out all the varied, authentic Tuscan cooking and dishes at the on-site restaurant. When we weren’t eating, we’d be lapping up drinks at Wendy’s bar. However, what we loved the most was chilling by the swimming pool, which sat in a lovely and serene garden surrounded by greenery. It was our favorite way and place to cool down. If you’re looking for that additional bit of activity, we highly suggest a quick game of tennis on the property, followed by a massage at the spa.

While the property had a bunch of charming digs, we ended up booking the extremely spacious Suite Castle, complete with a gorgeous four-poster bed and a discrete sitting area. Did we mention the bathtub in the luxe bathroom and the wine that would be delivered directly to our room? It really was the perfect way to end a day in Tuscany.

Badia a Coltibuono

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Oldest winery. One of Tuscany’s best winery hotels is Badia a Coltibuono, which looked like it came straight from a Raffaello painting. Today, this ancient Benedictine abbey-turned-winery hotel has a long and illustrious viticulture history. Did you know that a recent archaeological dig unearthed nearly two-millennia-old Romano-Etruscan grape seeds? Yes! If that wasn’t enough, the origins of the hotel go back to 1051, and it also happens to be the very first winery in all of Chianti. So, up here, it was all about unwinding and sipping on wine as time stood still.

The highlight here was the tasting excursions in the wine library, which also included some excellent organic olive oils made right on the property. Moreover, the advanced tasting excursions even included charcuterie and bruschetta. Furthermore, we even rested in the shaded cloisters, picnicked amongst the vineyards, and explored the ancient cantinas. We even enjoyed unique Tuscan cooking class experiences in the family’s historic kitchen. The standouts, though, were the magnificent Italian garden with the private hydromassage pool and the outdoor pool. If there was a place in all of Chianti where we could truly unwind and relax, it would be this verdant place.

Choose from a handful of rooms, which were the monks’ quarters originally, as well as four simple but spacious apartments. Not only did they have a bunch of modern comforts, but they also retained original features. Did we mention that they had Wi-Fi in all the common areas?

Borgo Pignano

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Set amidst 350 acres of olive groves and golden fields was Borgo Pignano, which is in Chianti and yet just 20 minutes from Volterra. However, it felt like a completely different world, especially with art galleries, stables, and a heart-stealer of a pool all on the property.

There was no dearth of amenities on the property. We spent our days wandering past the stables on the property, where the horses would graze lazily. There was even a yoga room, fitness center, and an art gallery tucked into an old stone building. Did we mention all the Chianti and pasta that we gorged on at both restaurants? Yes! Our favorite place was the swimming pool that overlooked the stunning landscape. We’d spend hours sprawled on the sun loungers under the parasols, with the staff serving us food and drinks right at our perch. The only time we moved from here was when Borgo Pignano Volterra’s Spa lured us in with its sauna and hammam.

While we had the choice of many amazing rooms and suites, our favorite was the one we chose, the Villa Suite, which had breathtaking views of the rolling hills and vineyards. Not just that, but the suite also had fresh fruits, a plush bed, and a luxe, frescoed bathroom, a polished piano, a flat-screen TV, and whatnot.

Colle Alberti Country House

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One of Tuscany’s best pool hotels is the Colle Alberti Country House, which is veritable proof that one doesn’t have to empty their bank accounts to stay at an amazing hotel. We’re talking about Colle Alberti Country House, which offers gorgeous views of the hazy Chianti hills, endless vineyards, and golden fields. Even though the estate is massive, the country house radiated a cozy, tucked-away vibe that made our stay extremely laidback and relaxing.

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First, we have to talk about the pool, which was not only slightly removed from the main estate but shared the same pastoral views of undulating hills, golden wheat fields, and vineyards. In fact, it was the perfect place to spend a leisurely afternoon swimming and by the water with a glass of wine. The real magic happened in the underground 17th-century wine cellars, which took the wine tasting to another level, especially with the well-crafted history lessons too. We’d wrap up the day with sunset cocktails in the garden before heading to the lounge bar, where dinner and yet another round of wine and cocktails were the perfect end to the day.

We had the choice of 18 rooms and suites, which were spread across the main house and the nearby barn and granary. The size made for a non-crowded but convivial Tuscan atmosphere. What’s more, every unit was a soothing blend of antique architecture and modern minimalism, allowing them to be luxurious but not ostentatious.

Castel Monastero

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If you’re on your honeymoon — first, second, or nth — then look no further than Castel Monastero, one of Tuscany’s best honeymoon hotels. Nestled inside a colossal 11th-century fortress-like monastery, the castle hotel made an immediate impression on us with the massive, dramatic wooden doors. Most of the 76 rooms and suites lie clustered around the main piazza, which is where you can see the rich history of this monastery fortress. The details are only such — think original beams, terracotta floors, and mesmerizing views out of the windows. Furthermore, the subtle details, moody decor, and a bevy of luxurious mod-cons like luxe bathrooms, bathtubs, and plush beds made the digs extremely romantic.

We were also impressed to no end by the amenities, especially the special saltwater pool, Aquae Monasterii, which was ideal for swimming in and lounging by with views no matter the time of the day. However, we’d usually be in the delightfully buzzing main square for aperitivo hour in the evenings. If that wasn’t enough, the restaurant even served an endless menu of delicious Tuscan creations. Last but not least, we were completely taken in by the enormous spa, where the only choice we actually had to make was whether to indulge in their detox programme or enjoy the local Chianti.

Castello di Fonterutoli

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Best overall. There’s more than one reason that Castello di Fonterutoli in Chianti is at the top of the list. Firstly, we legit lived like locals at this low-key yet lovely medieval village in the heart of the Chianti Classico estate of the Mazzeis family, who’ve been making wine here for a whopping 24 generations. When they turned their attention to hospitality, it resulted in Fonterutoli, which allowed us to experience life as a Tuscan local.

Secondly, what made us feel like a village resident rather than a guest was the low-key and yet attentive service, with the staff also helping us organize a bunch of activities. Think cooking classes, bike rentals, hiking, and even horse riding. Furthermore, the winery tour, which was the obvious highlight, included memorable tasting sessions. While the Osteria, which serves heritage dishes, has a more touristy vibe, it’s the local bar-café that we loved, as it welcomed both guests and locals. The standout for us, though, was the lovely swimming pool lying amidst olive groves, which was the perfect place. Besides free public parking, the standout for us was the swimming pool that lay amidst olive groves.

Choose from 16 rooms and suites and 4 traditional apartments, which will make you feel like you’re staying in a wealthy Italian friend’s palatial home! What’s more, they all were renovated but retained their old-world charm with vaulted ceilings, family antiques, terracotta floors, and mesmerizing views. Moreover, they even had modern touches, such as fireplaces, coffee tables, and sofas, and even traditional Tuscan-style lounges and kitchens.

Our Verdict!

While we loved all the stays in Chianti, the ones below are our favorites.

• Best overall: Castello di Fonterutoli
• Oldest winery: Badia a Coltibuono
• Best value for money: Castello di Bibbione
• Most luxurious: Borgo San Felice Resort Relais & Châteaux

Where to Stay in Chianti, Tuscany?

We begin with Greve in Chianti, a charming village that is the heart of the region and the perfect base for exploring it. Not only is there a wine museum, but it also has a unique triangular square, Piazza Giacomo Matteotti, where restaurants and wine bars serve typical Tuscan fare. Secondly, there’s Panzano, which is a mere 10-minute drive from Greve. This charming hilltop village is rich in authentic Tuscan charm, culture, and history, and also offers stunning views of the countryside. Its highlights include the Church of Santa Maria and the medieval Panzano Castle. The picturesque Radda is ideal for oenophiles and foodies, and in fact, is considered the capital of “Chianti Classico.”

The village of Castellina offers the perfect fusion of nature and history, but it’s most famous for the rampart walk, an elevated pathway hidden behind an ancient castle. Moreover, it also has cozy taverns, traditional shops, and a historic center and landmarks. Culture vultures will love the small fortified village of Volpaia for its exceptional organic wines, stone architecture, and tranquil atmosphere. Finally, there are Gaiole and Montefioralle, which are a historical village and one of the smallest and most enchanting of Italy’s villages.

Which is the best winery hotel in Chianti?

Some of the region’s best winery hotels are Borgo Scopeto Wine & Country Relais and Castello di Fonterutoli. 

Which is the most luxurious winery hotel in Chianti?

That would be the Borgo San Felice Resort Relais & Châteaux, which is one of the best Relais & Châteaux properties in the world.